Matches in SemOpenAlex for { <https://semopenalex.org/work/W2000642679> ?p ?o ?g. }
Showing items 1 to 95 of
95
with 100 items per page.
- W2000642679 endingPage "3686" @default.
- W2000642679 startingPage "3683" @default.
- W2000642679 abstract "Direct arylations of pyridine N-oxide (PyO), a convenient method to prepare 2-arylpyridines, catalyzed by Pd(OAc)(2) and PtBu(3) have been proposed to occur by the generation of a PtBu(3)-ligated arylpalladium acetate complex, (PtBu(3))Pd(Ar)(OAc) (1), and the reaction of this complex with PyO. We provide strong evidence that 1 does not react directly with PyO. Instead, our data imply that the cyclometalated complex [Pd(OAc)(tBu(2)PCMe(2)CH(2))](2), which is generated from the decomposition of 1, reacts with PyO and serves as a catalyst for the reaction of PyO with 1. The reaction of PyO with 1 occurs with an induction period, and the reaction of 1 with excess PyO in the presence of [Pd(OAc)(tBu(2)PCMe(2)CH(2))](2) is zeroth-order in 1. Moreover, the rates of reactions of PyO with bromobenzene catalyzed by [Pd(OAc)(tBu(2)PCMe(2)CH(2))](2) and [Pd(PtBu(3))(2)] depend on the concentration of [Pd(OAc)(tBu(2)PCMe(2)CH(2))](2) but not on the concentration of [Pd(PtBu(3))(2)]. Finally, the reaction of 1 with a model heteroarylpalladium complex containing a cyclometalated phosphine, [(PEt(3))Pd(2-benzothienyl)(tBu(2)PCMe(2)CH(2))], rapidly formed the arylated heterocycle. Together, these data imply that the rate-determining C-H bond cleavage occurs between PyO and the cyclometalated [Pd(OAc)(tBu(2)PCMe(2)CH(2))](2) rather than between PyO and 1. In this case, the resulting heteroarylpalladium complex transfers the heteroaryl group to 1, and C-C bond-formation occurs from (PtBu(3))Pd(Ar)(2-pyridyl oxide). This mechanism proposed for the direct arylation of PyO constitutes an example of C-H bond functionalization in which C-H activation occurs at one metal center and the activated moiety undergoes functionalization after transfer to a second metal center." @default.
- W2000642679 created "2016-06-24" @default.
- W2000642679 creator A5029098569 @default.
- W2000642679 creator A5085878716 @default.
- W2000642679 creator A5088865204 @default.
- W2000642679 date "2012-02-17" @default.
- W2000642679 modified "2023-10-01" @default.
- W2000642679 title "Mechanistic Studies on Direct Arylation of Pyridine <i>N</i>-Oxide: Evidence for Cooperative Catalysis between Two Distinct Palladium Centers" @default.
- W2000642679 cites W1969741970 @default.
- W2000642679 cites W1971378928 @default.
- W2000642679 cites W1980934047 @default.
- W2000642679 cites W1986353432 @default.
- W2000642679 cites W1993513558 @default.
- W2000642679 cites W2006758620 @default.
- W2000642679 cites W2011421576 @default.
- W2000642679 cites W2016755677 @default.
- W2000642679 cites W2038974680 @default.
- W2000642679 cites W2052111884 @default.
- W2000642679 cites W2055613358 @default.
- W2000642679 cites W2056258312 @default.
- W2000642679 cites W2065118662 @default.
- W2000642679 cites W2068644789 @default.
- W2000642679 cites W2088388835 @default.
- W2000642679 cites W2091897182 @default.
- W2000642679 cites W2096021030 @default.
- W2000642679 cites W2097184152 @default.
- W2000642679 cites W2110498029 @default.
- W2000642679 cites W2110930514 @default.
- W2000642679 cites W2146287537 @default.
- W2000642679 cites W2160889905 @default.
- W2000642679 cites W2323187930 @default.
- W2000642679 cites W2334536472 @default.
- W2000642679 cites W2950868506 @default.
- W2000642679 doi "https://doi.org/10.1021/ja2122156" @default.
- W2000642679 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3320665" @default.
- W2000642679 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22313324" @default.
- W2000642679 hasPublicationYear "2012" @default.
- W2000642679 type Work @default.
- W2000642679 sameAs 2000642679 @default.
- W2000642679 citedByCount "123" @default.
- W2000642679 countsByYear W20006426792012 @default.
- W2000642679 countsByYear W20006426792013 @default.
- W2000642679 countsByYear W20006426792014 @default.
- W2000642679 countsByYear W20006426792015 @default.
- W2000642679 countsByYear W20006426792016 @default.
- W2000642679 countsByYear W20006426792017 @default.
- W2000642679 countsByYear W20006426792018 @default.
- W2000642679 countsByYear W20006426792019 @default.
- W2000642679 countsByYear W20006426792020 @default.
- W2000642679 countsByYear W20006426792021 @default.
- W2000642679 countsByYear W20006426792022 @default.
- W2000642679 countsByYear W20006426792023 @default.
- W2000642679 crossrefType "journal-article" @default.
- W2000642679 hasAuthorship W2000642679A5029098569 @default.
- W2000642679 hasAuthorship W2000642679A5085878716 @default.
- W2000642679 hasAuthorship W2000642679A5088865204 @default.
- W2000642679 hasBestOaLocation W20006426792 @default.
- W2000642679 hasConcept C155647269 @default.
- W2000642679 hasConcept C161790260 @default.
- W2000642679 hasConcept C178790620 @default.
- W2000642679 hasConcept C185592680 @default.
- W2000642679 hasConcept C2779485729 @default.
- W2000642679 hasConcept C3044715 @default.
- W2000642679 hasConcept C502130503 @default.
- W2000642679 hasConceptScore W2000642679C155647269 @default.
- W2000642679 hasConceptScore W2000642679C161790260 @default.
- W2000642679 hasConceptScore W2000642679C178790620 @default.
- W2000642679 hasConceptScore W2000642679C185592680 @default.
- W2000642679 hasConceptScore W2000642679C2779485729 @default.
- W2000642679 hasConceptScore W2000642679C3044715 @default.
- W2000642679 hasConceptScore W2000642679C502130503 @default.
- W2000642679 hasIssue "8" @default.
- W2000642679 hasLocation W20006426791 @default.
- W2000642679 hasLocation W20006426792 @default.
- W2000642679 hasLocation W20006426793 @default.
- W2000642679 hasLocation W20006426794 @default.
- W2000642679 hasOpenAccess W2000642679 @default.
- W2000642679 hasPrimaryLocation W20006426791 @default.
- W2000642679 hasRelatedWork W1999313643 @default.
- W2000642679 hasRelatedWork W2148787175 @default.
- W2000642679 hasRelatedWork W2342086820 @default.
- W2000642679 hasRelatedWork W23791846 @default.
- W2000642679 hasRelatedWork W2395638556 @default.
- W2000642679 hasRelatedWork W2949133395 @default.
- W2000642679 hasRelatedWork W2951939317 @default.
- W2000642679 hasRelatedWork W2997339201 @default.
- W2000642679 hasRelatedWork W4220907498 @default.
- W2000642679 hasRelatedWork W4255827852 @default.
- W2000642679 hasVolume "134" @default.
- W2000642679 isParatext "false" @default.
- W2000642679 isRetracted "false" @default.
- W2000642679 magId "2000642679" @default.
- W2000642679 workType "article" @default.